4-(1,2,3-Thiadiazol-4-yl)benzaldehyde → 1-[4-(1,2,3-Thiadiazol-4-yl)phenyl]ethanol

HRID 216332Notes

Reaction equation

[CH3:1][Mg]Cl.[S:4]1[CH:8]=[C:7]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[N:6]=[N:5]1>O1CCCC1>[S:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH:13]([OH:14])[CH3:1])=[CH:15][CH:16]=2)[N:6]=[N:5]1

Participants

Conditions

Temperature: -78 °C

Procedure

Methylmagnesium chloride (3 M in tetrahydrofuran) (0.83 mL, 2.5 mmol) was added to a −78° C. solution of 4-(1,2,3-thiadiazol-4-yl)benzaldehyde (473 mg, 2.5 mmol) in tetrahydrofuran (10 mL). After stirring at −78° C. for 2 h, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 1-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanol.

Workup

customthe reaction mixture was quenched with saturated aqueous ammonium chloride
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9a84652538d347e2ac624294d371ab00
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

Loading…